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Find cheap Porter Airlines flights to Chicago from C$ 182

1 adult
0 bags
Wed 29/5
Wed 5/6

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Good to know

Low season

January

High season

August

Cheapest flight

C$ 182

Average price round-trip

C$ 341

Good deal round-trip

C$ 311

Good deal one-way

C$ 177
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Island to Chicago Midway Airport
(avg. price over the last 2 weeks)
or less
or less

When to book flights with Porter Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Porter Airlines

  • Is Porter Airlines cheaper than other airlines flying to Chicago?

    Porter Airlines is currently the only airline with deals flying to Chicago, with an average return price of C$ 250.

  • Which other airlines fly to Chicago?

    Along with Porter Airlines, you can also fly to Chicago with United Airlines.

  • How much is a flight to Chicago with Porter Airlines?

    On average, Porter Airlines flights to Chicago cost C$ 154 for one-way and C$ 250 return.

  • Which airport do Porter Airlines flights to Chicago fly into?

    Porter Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

See more FAQs

Top tips for your flights to Chicago with Porter Airlines

  • Looking to fly from Canada to Chicago with Porter Airlines? 25% of our users found flights for the following prices or less: From Toronto Island Airport C$ 177 one-way, C$ 311 round-trip.
  • The cheapest flight to Chicago with Porter Airlines found on KAYAK in the last 2 weeks departed from Toronto Island Airport and cost C$ 172.

Porter Airlines customer reviews

7.4
GoodBased on 436 verified guest reviews
7.6Boarding
7.4Food
6.6Entertainment
7.5Comfort
8.2Crew
Traveler rating:
Sort by:
A
8.0 Very good
Pros:Crew is very polite and helpful. The truffles are awesome!
Cons:Frequent delays
A
9.2 Wonderful
Pros:due to weather then mechanical difficulty, we were quite delayed in take off, but the boarding area was comfortable and the airline did everything they could make our connection possible and we though delayed landed in Sault Ste. Marie that day. Not ideal, but admirable.
A
10.0 Wonderful
Pros:Ease of boarding. Carry on luggage is handled by crew staff - makes boarding much easier as passengers aren't struggling to find space for the carry on bags. The bags are ready for pickup upon exiting the aircraft. Would highly recommend Porter and would use again.
Cons:Flight was approx. 10 minutes late, but the time was made up during the flight.
A
9.6 Wonderful
Pros:it was such a smooth flight
Cons:all good
J
2.0 Poor
Pros:Nothing
Cons:I arrived to the checkout desk line @ 1:20pm and there was no attendant available. The attendant from the adjacent airline attempted to help me as best she could but to no avail she was unable to reach anyone at gate. I finally was directed to the information desk @1:45pm in which case the receptionist tried his best to help me board the plane and was told the plane already left despite the fact the departure time was 2:30pm. After calling Porter Airlines I was emotional distraught and upset. Not only was it my birthday but the airline refused to assist in giving me some sort of discount or fair adjustment I also never checked in my hotel reservations losing more money. The porter associate was RUDE and refused to transfer me to his Supervisor. He told the supervisor left @3:30pm and won't be back until 8pm. After calling the airline again I was told the insurance I purchased with my flight was invalid.
A
4.8 Mediocre
Cons:Flight was very delayed. We got turned around in flight and then ultimately made it. No apologies from crew or porter.
A
4.3 Mediocre
Pros:Lounge, flight, flight service
Cons:90 min late take off.
A
8.0 Very good
Pros:Excellent service
Cons:Delay
A
6.0 Okay
Pros:Efficient
Cons:Late flight
A
5.6 Fair
Cons:Flight was delayed.
Read more about Porter Airlines

Book Cheap flights with Porter Airlines to Chicago

Recent round-trip flight deals

22/5Wed
directPorter Airlines
1h 47mYTZ-MDW
26/5Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 313
24/5Fri
directPorter Airlines
1h 47mYTZ-MDW
27/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 314
13/6Thu
directPorter Airlines
1h 47mYTZ-MDW
17/6Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 315
7/6Fri
directPorter Airlines
1h 47mYTZ-MDW
17/6Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 317
27/5Mon
directPorter Airlines
1h 47mYTZ-MDW
5/6Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 320
24/5Fri
directPorter Airlines
1h 47mYTZ-MDW
27/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 325
29/5Wed
directPorter Airlines
1h 47mYTZ-MDW
4/6Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 326
12/5Sun
directPorter Airlines
1h 47mYTZ-MDW
31/5Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 328
23/5Thu
directPorter Airlines
1h 47mYTZ-MDW
26/5Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 330
13/5Mon
directPorter Airlines
1h 47mYTZ-MDW
14/5Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 335
28/5Tue
1 stopPorter Airlines
5h 52mYUL-MDW
4/6Tue
1 stopPorter Airlines
4h 35mMDW-YUL
C$ 335
13/5Mon
directPorter Airlines
1h 47mYTZ-MDW
13/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 336
20/5Mon
1 stopPorter Airlines
4h 27mYUL-MDW
23/5Thu
1 stopPorter Airlines
4h 45mMDW-YUL
C$ 336
13/5Mon
directPorter Airlines
1h 47mYTZ-MDW
23/5Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 337
28/5Tue
1 stopPorter Airlines
4h 07mYUL-MDW
30/5Thu
1 stopPorter Airlines
3h 55mMDW-YUL
C$ 337
28/5Tue
directPorter Airlines
1h 47mYTZ-MDW
1/6Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 339
20/5Mon
1 stopPorter Airlines
6h 32mYUL-MDW
22/5Wed
1 stopPorter Airlines
3h 55mMDW-YUL
C$ 339
29/5Wed
directPorter Airlines
1h 47mYTZ-MDW
31/5Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 340
20/5Mon
1 stopPorter Airlines
4h 27mYUL-MDW
25/5Sat
1 stopPorter Airlines
5h 35mMDW-YUL
C$ 340
26/5Sun
directPorter Airlines
1h 47mYTZ-MDW
27/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 341

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Recent one-way flight deals

12/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 182
14/6Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 184
18/6Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 186
21/5Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 187
27/5Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 190
29/5Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 199
19/5Sun
1 stopPorter Airlines
6h 37mYUL-MDW
C$ 205
18/6Tue
1 stopPorter Airlines
6h 22mYUL-MDW
C$ 209
13/5Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 210
28/5Tue
1 stopPorter Airlines
6h 32mYUL-MDW
C$ 210
12/5Sun
directPorter Airlines
1h 47mYTZ-MDW
C$ 212
24/5Fri
1 stopPorter Airlines
4h 27mYUL-MDW
C$ 214
5/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 216
3/6Mon
1 stopPorter Airlines
4h 07mYUL-MDW
C$ 220
23/6Sun
directPorter Airlines
1h 47mYTZ-MDW
C$ 227
4/9Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 232
20/5Mon
1 stopPorter Airlines
6h 32mYUL-MDW
C$ 232
11/5Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 233
23/7Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 238
28/6Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 240

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Search by price

Flights to Chicago - Porter Airlines

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 987
First Class flights to Chicago
C$ 827
Business Class flights to Chicago
C$ 542
C$ 279

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